A headwear insert system is provided comprising a headwear insert having a planar multilayered substrate with a first side and a second side. The planar multilayered substrate may comprise a substantially oblong shape with a rounded plateau protruding from a top portion of the planar multilayered substrate. The planar multilayered substrate may further comprise a polyester mesh layer, a stabilizing layer, an absorptive layer and a neoprene layer. The stabilizing layer and the absorptive layer may be disposed between the polyester mesh layer and the neoprene layer. A seam may couple the polyester mesh layer and the neoprene layer together. The stabilizing layer and the absorptive layer may not be coupled to the seam, the polyester mesh layer nor the neoprene layer.